CN101727027B - Electrophotographic photoreceptor and image forming apparatus with the same - Google Patents
Electrophotographic photoreceptor and image forming apparatus with the same Download PDFInfo
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- CN101727027B CN101727027B CN2009101690836A CN200910169083A CN101727027B CN 101727027 B CN101727027 B CN 101727027B CN 2009101690836 A CN2009101690836 A CN 2009101690836A CN 200910169083 A CN200910169083 A CN 200910169083A CN 101727027 B CN101727027 B CN 101727027B
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Abstract
The present invention realizes an electrophotographic photoreceptor and an image forming apparatus with the same. The electrophotographic photoreceptor of the invention is provided with a conductive substrate and a photosensitive layer formed on the conductive substrate. The photosensitive layer comprises charge generating agent, charge conveying agent with hole conveying agent, and binding resion. The invention is characterized in that the hole conveying agent comprises enamine compound represented by a general formula (1a) or (1b). In the formula (1a), Ra1 is a substituted or unsubstituted aryl with 6-30 carbon atoms; R2-R6 are same or different, are hydrogen atoms, alkyls with 1-12 carbon atoms each, or aryls with 6-30 carbon atoms; m, n and o are integers selected from 1-4. In the formula (1b), Rb1 is a substituted or unsubstituted aryl with 6-30 carbon atoms; R2-R6 are same or different from one another, are hydrogen atoms, alkyls with 1-12 carbon atoms each, or aryls with 6-30 carbon atoms; p, q and r are integers selected from 1-4.
Description
Technical field
The present invention relates to Electrophtography photosensor and possess its image processing system.
Background technology
At present, as the Electrophtography photosensor that in image processing system etc., uses, known have conductive base and an Electrophtography photosensor that is arranged on the photographic layer on this conductive base.In addition, in recent years, to the Electrophtography photosensor that suppresses the electric leakage degree, proposed between conductive base and photographic layer, to sandwich the Electrophtography photosensor in middle layer as insulation.
As this Electrophtography photosensor; Use the Organophotoreceptor that constitutes photographic layer by organism widely, this photographic layer contain through rayed produce electric charge charge generating, carry the charge transport agent of the electric charge that produces and make charge generating and the charge transport agent disperses and cambial binding resin.
The charge transport agent that is used for Organophotoreceptor has the electron transporting agent and the cavity conveying agent of carrying the hole of conveying electronic.Wherein, as the cavity conveying agent, use hydrazone compound, stilbene compounds, enamine compound etc. in recent years, but may not be the compound that satisfies the cavity conveying ability.Therefore, be difficult to obtain having the Electrophtography photosensor of sufficient electrical characteristics.
So, in order to solve the problem of this cavity conveying ability, as the excellent cavity conveying agent of mobility, the enamine compound of ad hoc structure is for example disclosed in the patent documentation 1.
Patent documentation 1: No. 2812618 communique of Jap.P.
But the enamine compound of record in the patent documentation 1 is because substituent A, B are independent substituent, be destroyed as the planarity of compound, so pi-electron is difficult to resonance stabilization, can not get sufficient mobility.Therefore, when using the enamine compound of record in the patent documentation 1, can not get good light sensitivity as the cavity conveying agent of Electrophtography photosensor.
Summary of the invention
The present invention is In view of the foregoing and proposes, and its purpose is, realizes the Electrophtography photosensor of ISO and possesses its image processing system.
Promptly; Electrophtography photosensor of the present invention has conductive base and is formed on the photographic layer on the said conductive base; This photographic layer contains charge generating, contains the charge transport agent and the binding resin of cavity conveying agent; It is characterized in that, said cavity conveying agent contain formula (1a) or (1b) shown in enamine compound
In the formula (1a), Ra
1For having or not having the aryl of substituent carbon number 6～30, Ra
2～Ra
6Identical or different respectively; For the alkyl of hydrogen atom, carbon number 1～12 or have or do not have the aryl of substituent carbon number 6～30; Said substituting group is the alkyl of carbon number 1～12 or the alkoxy of carbon number 1～12, and m, n, the o of expression substituting group repeat number is 1～4 integer
In the formula (1b), Rb
1Has or do not have the aryl of substituent carbon number 6～30, Rb
2～Rb
6Identical or different respectively; For the alkyl of hydrogen atom, carbon number 1～12 or have or do not have the aryl of substituent carbon number 6～30; Said substituting group is the alkyl of carbon number 1～12 or the alkoxy of carbon number 1～12, and p, q, the r of expression substituting group repeat number is 1～4 integer.
Further, said general formula (1a) and (1b) in Ra
1, Rb
1For having the aryl of substituent carbon number 6～30, Ra
2, Ra
3, Rb
2, Rb
3Be the aryl of carbon number 6～30, Ra
5, Ra
6, Rb
5, Rb
6Be hydrogen atom.
Further, said photographic layer is at the single layer structure that contains said charge generating, said charge transport agent and said binding resin with one deck.
In addition, in the photographic layer of said single layer structure, with respect to said binding resin 100 mass parts, the content of said cavity conveying agent is 20～500 mass parts.
In addition, said photographic layer is a laminar structure, has: contain the charge generating layer of said charge generating at least and contain the charge transport layer of said charge transport agent and said binding resin.
In addition, in the photographic layer of said laminar structure, with respect to said binding resin 100 mass parts, the content of said cavity conveying agent is 10～500 mass parts.
In addition, image processing system of the present invention is characterized in that, possesses Electrophtography photosensor of the present invention.
The light sensitivity of Electrophtography photosensor of the present invention is high.
Description of drawings
Fig. 1 has the structural representation of mono-layer electronic photographic photoreceptor of the photographic layer of single layer structure for expression;
Fig. 2 has the structural representation of laminated electrophotographic photoreceptor of the photographic layer of laminar structure for expression;
Fig. 3 is the structural representation of an example of expression image processing system of the present invention.
Symbol description
10 image processing systems
11 Electrophtography photosensors
12 charged elements
13 exposing units
14 developer rolls
15 transfer rolls
16 cleaning units
Embodiment
The inventor finds, through when preparing the cavity conveying agent, improves the substituent planarity of enamine compound, and pi-electron is prone to resonance stabilization, obtains the high cavity conveying agent of mobility.Further find, use the light sensitivity height of the Electrophtography photosensor of this cavity conveying agent manufacturing, so far accomplished the present invention.
Promptly; Electrophtography photosensor of the present invention has conductive base and is formed on the photographic layer on the above-mentioned conductive base; This photographic layer contains charge generating, contains the charge transport agent and the binding resin of cavity conveying agent; It is characterized in that, above-mentioned cavity conveying agent contain formula (1a) or (1b) shown in enamine compound.
In the formula (1a), Ra
1Be the aryl of carbon number 6～30, Ra
2～Ra
6Identical or different respectively, be the alkyl of hydrogen atom, carbon number 1～12 or the aryl of carbon number 6～30, m, n, the o of expression substituting group repeat number is 1～4 integer.
In the formula (1b), Rb
1Be the aryl of carbon number 6～30, Rb
2～Rb
6Identical or different respectively, be the alkyl of hydrogen atom, carbon number 1～12 or the aryl of carbon number 6～30, p, q, the r of expression substituting group repeat number is 1～4 integer.
[Electrophtography photosensor]
Electrophtography photosensor of the present invention is formed with the photographic layer that contains charge generating, charge transport agent and binding resin on conductive base.
< conductive base >
As the material of conductive base, can enumerate for example metals such as iron, aluminium, copper, tin, platinum, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, palladium, indium, stainless steel and brass, this metal is formed the material of oxidation overlay film through anodized; Vapor deposition or lamination the plastic material of this metal; Glass with coverings such as silver iodide, tin oxide, indium oxides; Disperseed the plastic material of electrically conductive microparticles such as carbon black etc.
And in the present invention, " (having) electric conductivity " refers to resistivity value is 1.0 * 10
8Below the Ω cm.
As the shape of conductive base, can enumerate sheet, drum type etc.The shape of conductive base can suitably be confirmed according to the structure of image processing system.
Conductive base can also be implemented roughened to its surface.Thus, can prevent to produce interference fringe.As the method for roughened, can enumerate etching, anodic oxidation, wet blasting method, sand-blast, rough cut, not be in the mood for methods such as cutting.
< photographic layer >
Photographic layer contains charge generating, charge transport agent and binding resin.
(charge generating)
As charge generating, can use known charge generating.Specifically, can enumerate organic light-guide electricity bodies such as phthualocyanine pigment, perylene series pigments, disazo pigment, diketopyrrolo-pyrrole pigment, no metal naphthalene phthalocyanine pigment, metal naphthalene phthalocyanine pigment, square acid color (squaraine pigment), trisazo pigment, indigo pigment, azulenes pigment (azulenium pigment), phthalocyanine pigments, pyrans pigment, anthanthrone pigment, triphenylmethane series pigments, intellectual circle's pigment, toluidine series pigments, pyrazoline series pigments, quinacridone pigment; Inorganic smooth conductive agents such as selenium, selenium-tellurium, selenium-arsenic, cadmium sulfide, amorphous silicon etc.Charge generating can be used a kind of separately, also can be also with two or more.
In addition, as charge generating, be preferably compound (11-1)～(11-4).
(charge transport agent)
The charge transport agent contains the cavity conveying agent.
The invention is characterized in, the cavity conveying agent contain above-mentioned general formula (1a) or (1b) shown in enamine compound.Below, the compound shown in the general formula (1a) is designated as compound (1a).Compound shown in the general formula (1b) is designated as compound (1b).
Ra
1, Rb
1Be respectively the aryl of carbon number 6～30.As aryl, can enumerate phenyl, tolyl, xylyl, 2,4,6-trimethylphenyl, naphthyl, anthryl, phenanthryl etc.
Ra
2～Ra
6, Rb
2～Rb
6Identical or different respectively, be the alkyl of hydrogen atom, carbon number 1～12 or the aryl of carbon number 6～30.As alkyl, can enumerate methyl, ethyl, propyl group, isopropyl, normal-butyl, the tert-butyl group, amyl group, isopentyl, neopentyl, hexyl, heptyl, octyl group, nonyl, decyl, undecyl, dodecyl etc.As aryl, can enumerate phenyl, tolyl, xylyl, 2,4,6-trimethylphenyl, naphthyl, anthryl, phenanthryl etc.
The aryl of carbon number 6～30 can have substituting group, as substituting group, is preferably the alkyl of carbon number 1～12 or the alkoxy of carbon number 1～12.As the alkyl of carbon number 1～12, can enumerate the substituting group same with above-mentioned substituting group.As the alkoxy of carbon number 1～12, can enumerate methoxyl, ethoxy, positive propoxy, isopropoxy, n-butoxy, just own oxygen base, 2-methyl amoxy, 2,2,2-trifluoro ethoxy, 2,2,3,3,3-five fluorine propoxyl group etc.
Ra
1, Rb
1Be preferably and have substituent aryl, substituting group is preferably alkoxy.Ra
2, Ra
3, Rb
2, Rb
3Be preferably the aryl of carbon number 6～30, further be preferably phenyl.Ra
5, Ra
6, Rb
5, Rb
6Be preferably hydrogen atom.
As compound (1a), can enumerate for example compound (1-1)～(1-3).And, in this manual, only use the line segment outstanding partly to represent the methyl with the carbon atom bonding of phenyl ring sometimes from the hexagonal summit of representing phenyl ring.
Compound (1a) for example is prepared as follows.Ra in the reaction equation
1～Ra
6, m, n be identical with the explanation of formula (1a) with o.
Operation (a):
After making compound (31) and triethyl phosphite (32) reacting generating compound (33), unreacted triethyl phosphite (32) is removed in decompression distillation.
The reaction ratio (mol ratio) of compound (31) and triethyl phosphite (32) is preferably 1: 1～and 1: 2.5.If triethyl phosphite (32) is very few, then because the compound (31) of remained unreacted is difficult to carry out purifying.If triethyl phosphite (32) is too much, then preparation cost improves.Temperature of reaction is preferably 160 ℃～200 ℃, and the reaction time is preferably 2 hours～and 10 hours.Through in this scope, can implement required reaction effectively to prepare equipment more easily.
Operation (b):
Through in the presence of alkali, make compound (33) and compound (34) in solvent behind the reacting generating compound (35), to compound (35) extract, purifying.
The reaction ratio (mol ratio) of compound (33) and compound (34) is preferably 0.5: 1～and 1: 2.5.If compound (33) is very few, then the harvest yield of compound (35) reduces.If compound (33) is too much, then unreacted compound (33) increases, because subsidiary reaction etc. might be difficult to carry out the purifying of compound (35).
Temperature of reaction is preferably-20 ℃～30 ℃, and the reaction time is preferably 5 hours～and 30 hours.Through in this scope, can implement required reaction effectively to prepare equipment more easily.
As alkali, can enumerate for example sodium alkoxide such as sodium methoxide, caustic alcohol, metal hydrides such as sodium hydride, hydrofining, slaines such as n-BuLi etc.Alkali can use a kind of separately, also can make up two or more the use.
With respect to (34) 1 moles of compounds, the addition of alkali is preferably 0.8～1.5 mole.The addition of alkali is during less than 0.8 mole, and compound (33) might significantly reduce with the reactivity of compound (34).If the addition of alkali surpasses 1.5 moles, then might be difficult to control the reaction of compound (33) and compound (34).
As solvent, can enumerate for example ethers such as diethyl ether, tetrahydrofuran 、 diox; Halogenated hydrocarbons such as methylene chloride, chloroform, ethylene dichloride; Aromatic hydrocarbons such as benzene, toluene, dimethyl formamide etc.
Operation (c): through in the presence of catalyzer etc., make compound (35) and compound (36) in solvent behind the reacting generating compound (37), to compound (37) extract, purifying.
The reaction ratio (mol ratio) of compound (35) and compound (36) is preferably 1: 1～and 1: 1.5.If compound (36) is very few, then the harvest yield of compound (37) reduces.If compound (36) is too much, then unreacted compound (36) increases, because subsidiary reaction etc. might be difficult to carry out the purifying of compound (37).
Temperature of reaction is preferably 80 ℃～140 ℃, and the reaction time is preferably 2 hours～and 10 hours.Through in this scope, can implement required reaction effectively to prepare equipment more easily.
As catalyzer, can enumerate for example palladium series catalyst etc.As palladium series catalyst, can enumerate three (dibenzalacetones), two palladiums (0) etc.Catalyzer can use a kind of separately, also can make up two or more the use.
As solvent, can enumerate for example xylene etc.
Operation (d):
Through in the presence of acid catalyst etc., make secondary amine compound (37) and aldehyde compound (38) in solvent behind the reacting generating compound (1a), to compound (1a) extract, purifying.
The reaction ratio (mol ratio) of secondary amine compound (37) and aldehyde compound (38) is preferably 1: 1～and 1: 2.5.If aldehyde compound (38) is very few, then residual secondary amine compound (37) therefore is difficult to carry out purifying.If aldehyde compound (38) is too much, then preparation cost improves.
Temperature of reaction is preferably 60 ℃～150 ℃, and the reaction time is preferably 1 hour～and 5 hours.Through in this scope, can implement required reaction effectively to prepare equipment more easily.
As acid catalyst, can enumerate for example p-toluenesulfonic acid, camphorsulfonic acid, p-toluenesulfonic acid pyridine etc.
With respect to aldehyde compound (38) 100 mass parts, the addition of acid catalyst is preferably 0.05～10 mass parts, more preferably 0.2～4 mass parts.The addition of acid catalyst is during less than 0.05 mass parts, and secondary amine compound (37) might significantly reduce with the reactivity of aldehyde compound (38).If the addition of acid catalyst surpasses 10 mass parts, then might be difficult to control the reaction of secondary amine compound (37) and aldehyde compound (38).
As solvent, can enumerate for example toluene, xylene, chlorobenzene, butanols, diethylene glycol dimethyl ether etc.
As compound (1b), can enumerate for example compound (1-4)～(1-6).
Compound (1b) for example is prepared as follows.Rb in the reaction equation
1～Rb
6, p, q be identical with the explanation of formula (1b) with r.
Operation (a): after making compound (41) and triethyl phosphite (32) reacting generating compound (43), unreacted triethyl phosphite (32) is removed in decompression distillation.Particular content is identical with the operation (a) of the synthetic example of above-claimed cpd (1a).
Operation (b):
Through in the presence of alkali, make compound (43) and compound (44) in solvent behind the reacting generating compound (45), to compound (45) extract, purifying.
The reaction ratio (mol ratio) of compound (43) and compound (44) is preferably 1: 1～and 1: 2.5.If compound (43) is very few, then the harvest yield of compound (45) reduces.If compound (43) is too much, then unreacted compound (43) increases, because subsidiary reaction etc. might be difficult to carry out the purifying of compound (45).
Temperature of reaction, reaction time preferably with the same scope of the operation (b) of the synthetic example of compound (1a) in.
As alkali, solvent, can enumerate the same kind of operation (b) with the synthetic example of compound (1a).The addition of alkali preferably with the same scope of the operation (b) of the synthetic example of compound (1a) in.
Operation (c): through in the presence of catalyzer etc., make compound (45) and compound (46) in solvent behind the reacting generating compound (47), to compound (47) extract, purifying.
The reaction ratio (mol ratio) of compound (45) and compound (46) is preferably 1: 1～and 1: 1.5.If compound (46) is very few, then the harvest yield of compound (47) reduces.If compound (46) is too much, then unreacted compound (47) increases, because subsidiary reaction etc. might be difficult to carry out the purifying of compound (47).
Temperature of reaction, reaction time preferably with the same scope of the operation (c) of the synthetic example of compound (1a) in.
As catalyzer, can enumerate the same kind of operation (c) with the synthetic example of compound (1a).As solvent, can enumerate for example xylene etc.
Operation (d):
Through in the presence of acid catalyst etc., make secondary amine compound (47) and aldehyde compound (48) in solvent behind the reacting generating compound (1b), to compound (1b) extract, purifying.
The reaction ratio (mol ratio) of secondary amine compound (47) and aldehyde compound (48) is preferably 1: 1～and 1: 2.5.If aldehyde compound (48) is very few, then residual secondary amine compound (47) therefore is difficult to carry out purifying.If aldehyde compound (48) is too much, then preparation cost improves.
Temperature of reaction, reaction time preferably with the same scope of the operation (d) of the synthetic example of compound (1a) in.
As acid catalyst, solvent, can enumerate the same kind of operation (d) with the synthetic example of compound (1a).The addition of acid catalyst preferably with the same scope of the operation (d) of the synthetic example of compound (1a) in.
About the compound (1a) of above explanation or (1b), because compound is a planar structure, pi-electron is prone to resonance, is prone to produce electron mobility.Therefore, through containing compound (1a) at photographic layer or, obtaining the Electrophtography photosensor of the excellent ISO of electrical characteristics (1b) as the cavity conveying agent.
The charge transport agent can roughly be divided into cavity conveying agent and electron transporting agent.Among the present invention, use above-claimed cpd (1a) or, still can also and use cavity conveying agent, electron transporting agent in addition (1b) as the cavity conveying agent.
In other the charge transport agent; As the cavity conveying agent, can enumerate biphenylamine based compound, phenylenediamine based compound, naphthylenediamine based compound, luxuriant and rich with fragrance two amine compounds, oxadiazole based compound, styryl based compound, carbazole based compound, pyrazoline based compound, hydrazone based compound, triphenylamine based compound, indoles based compound, oxazole based compound, isoxazole based compound, thiazole compound, thiadiazoles based compound, imidazole compound, pyrazoles based compound, three azole compounds, butadiene-based compound, pyrene-hydrazone based compound, acryl aldehyde based compound, carbazole-hydrazone based compound, quinoline-hydrazone based compound, Stilbene based compound, Stilbene-hydrazone based compound and two phenylenediamine based compounds etc.The cavity conveying agent can be used a kind of separately, also can be also with two or more.
On the other hand; As electron transporting agent; Can enumerate quinone derivatives, anthraquinone derivative, malononitrile derivant, thiapyran derivant, trinitro-thioxanthone derivates, 3; 4,5,7-tetranitro-9-fluorenone derivatives, dinitro anthracene derivant, dinitro acridine derivatives, nitroanthraquinone derivant, dinitroanthraquinone derivant, tetracyanoethylene, 2; 4,8-trinitro-thioxanthones, dinitro benzene, dinitro anthracene, dinitro acridine, nitroanthraquinone, dinitroanthraquinone, succinic anhydride, maleic anhydride, dibrominated maleic anhydride etc.Electron transporting agent can be used a kind of separately, also can make up two or more the use.
In these electron transporting agent, from electronics acceptance and good with the coupling of charge generating, the Electrophtography photosensor aspect that obtains light sensitivity characteristic and excellent in te pins of durability is considered, is preferably compound (12-1)～(12-4) especially.
(binding resin)
As binding resin, can enumerate the thermoplastic resin such as polycarbonate resin, polyarylate resin, SB, styrene-acrylonitrile copolymer, styrene-maleic acid copolymer, acrylic copolymer, styrene-propene acid copolymer, polyvinyl resin, vinyl-vinyl acetate copolymer, chlorinated polyethylene resin, Corvic, acrylic resin, ionomer resin, vinyl chloride vinyl acetate copolymer, alkyd resin, polyamide, urethane resin, polysulfone resin, diallyl phthalate ester resin, ketone resin, polyvinyl acetal resin, polyvinyl butyral resin, polyether resin of bisphenol Z type, bisphenol Z C type, bisphenol-c type, bisphenol A-type etc.; Heat-curing resins such as organic siliconresin, epoxy resin, phenolics, carbamide resin, melamine resin; Light-cured type such as epoxy acrylate, polyurethane-acrylate resin etc.Binding resin can use a kind of separately, also can be also with two or more.
In these binding resins, from the film strength of photographic layer, consider, be preferably compound (13-1) especially with the viewpoint of the intermiscibility of cavity conveying agent and electron transporting agent.
(other)
The electrofax characteristic not being brought in the scope of influence, can also contain known adjuvant in the photographic layer.As adjuvant, can enumerate for example anti-deterioration agent, softening agent, plastifier, surface modifier, extender, tackifier, dispersion stabilizer, wax, acceptor, donors etc. such as anti-oxidant, light stabilizer, free radical scavenger, singlet quencher (singlet quencher), ultraviolet light absorber.
In addition, in order to improve the light sensitivity of photoreceptor, also can be with charge generating and with for example known sensitizers such as terphenyl, naphthalene halide quinones, acenaphthene.
As these adjuvants, can enumerate biphenol compound, anti-oxidant particularly.Through adding biphenol compound, can suppress the generation of crackle, prevent that photographic layer from splitting.Through adding anti-oxidant, can suppress charged potential and reduce.
< structure of photographic layer >
Photographic layer can be at the single layer structure that contains above-mentioned charge generating, charge transport agent and binding resin with one deck, can also be for having the charge generating layer that contains charge generating at least and containing the laminar structure of the charge transport layer of charge transport agent and binding resin.(a) among Fig. 1 is for being illustrated in the structural representation that is formed with on the conductive base 120 at the mono-layer electronic photographic photoreceptor 100 of the photographic layer 140 that contains charge generating, charge transport agent and binding resin with one deck.(a) among Fig. 2 is formed with the charge generating layer 240 that contains charge generating and contains the structural representation of the charge transport layer 220 of charge transport agent and binding resin as the laminated electrophotographic photoreceptor 200 of the photographic layer 140 ' of laminar structure for being illustrated on the conductive base 120.
And, to the lamination order not especially restriction of the charge generating layer in the photographic layer 140 ' of laminar structure 240 with charge transport layer 220.But,,, charge transport layer 220 is set on charge generating layer 240 preferably in order to protect charge generating layer 240 because the Film Thickness Ratio charge transport layer 220 of charge generating layer 240 is thin.
(photographic layer of single layer structure)
With respect to binding resin 100 mass parts, the content of charge generating is preferably 0.1～50 mass parts, 0.5～30 mass parts more preferably.
With respect to binding resin 100 mass parts, the content of cavity conveying agent is preferably 20～500 mass parts, 30～200 mass parts more preferably.
With respect to binding resin 100 mass parts, the content of electron transporting agent is preferably 5～100 mass parts, 10～80 mass parts more preferably.
The thickness of photographic layer 140 is preferably 5～100 μ m, more preferably 10～50 μ m.
(photographic layer of laminar structure)
With respect to binding resin 100 mass parts, the content of the charge generating in the charge generating layer 240 is preferably 5～1000 mass parts, 30～500 mass parts more preferably.The thickness of charge generating layer 240 is preferably 0.01～5 μ m, more preferably 0.1～3 μ m.
With respect to binding resin 100 mass parts, the content of the cavity conveying agent of charge transport layer 220 is preferably 10～500 mass parts, 25～200 mass parts more preferably.
When charge transport layer 220 contained electron transporting agent, with respect to binding resin 100 mass parts, the content of electron transporting agent was preferably 5～200 mass parts, 10～100 mass parts more preferably.
The thickness of charge transport layer 220 is preferably 2～100 μ m, more preferably 5～50 μ m.
< other layer >
In the Electrophtography photosensor of the present invention, can also be at conductive base 120 and photographic layer 140, sandwich middle layer 160 ((b) of Fig. 1, (b) of Fig. 2) between 140 '.Mono-layer electronic photographic photoreceptor 100 or the laminated electrophotographic photoreceptor 200 that sandwiches middle layer 160 can suppress the generation of leaking electricity effectively.In addition, protective seam 180 (showing in only to (c) of photographic layer 140 at Fig. 1) can also be set on photographic layer 140,140 '.
Inorganic particulate is contained in middle layer 160.Through containing inorganic particulate, the generation that can suppress to leak electricity, and when mono-layer electronic photographic photoreceptor 100 or laminated electrophotographic photoreceptor 200 are made public circulating current successfully, thereby can suppress the rising of resistance.Metal or metal oxide can be enumerated as inorganic particulate, specifically aluminium, iron, copper, titanium dioxide, silicon dioxide, aluminium oxide, zirconia, tin oxide, zinc paste, indium oxide etc. can be enumerated.Wherein, be preferably titanium dioxide.Particularly consider, be preferably Titanium Dioxide Rutile Top grade from the viewpoint that can give appropriate insulativity.
Binding resin is also contained in middle layer 160 except above-mentioned inorganic particulate.As binding resin, can from the binding resin of previous example, select more than one to use.
The thickness in middle layer 160 is preferably 0.1～10 μ m, more preferably 0.5～5 μ m.With respect to binding resin 100 mass parts, the content of the inorganic particulate in the middle layer 160 is preferably 10～1000 mass parts, 30～400 mass parts more preferably.
< manufacturing of Electrophtography photosensor >
Electrophtography photosensor of the present invention for example can be made as follows.
(mono-layer electronic photographic photoreceptor)
The electron transporting agent of in solvent, dissolving or being dispersed with cavity conveying agent, charge generating, binding resin and adding as required; After being coated on the coating fluid that obtains therefrom on the conductive base 120; Carry out drying, thereby be manufactured on the mono-layer electronic photographic photoreceptor 100 that is formed with photographic layer 140 on the conductive base 120.
The preparation of coating fluid is through using roller mill, bowl mill, vertical ball mill, coating vibrator, ultrasonic dispersing machine etc., and dissolving or dispersion respectively become to assign to carry out in solvent.
As solvent, can enumerate for example alcohols such as methyl alcohol, ethanol, isopropyl alcohol, butanols; Aliphatic hydrocarbons such as normal hexane, octane, cyclohexane; Aromatic hydrocarbons such as benzene,toluene,xylene; Halogenated hydrocarbons such as methylene chloride, ethylene dichloride, chloroform, phenixin, chlorobenzene; Ethers such as dimethyl ether, diethyl ether, tetrahydrofuran, glycol dimethyl ether, diethylene glycol dimethyl ether; Ketones such as acetone, butanone, cyclohexanone; Ester such as ethyl acetate, methyl acetate class; Dimethylformaldehyde, dimethyl formamide, dimethyl sulfoxide etc.Solvent can use a kind of separately, also can mix two or more the use.
Coating process can be enumerated dip coating, spraying process, spin-coating method, coiling rod rubbing method known method such as (bar coating).As drying device, can enumerate high-temperature drier, drying under reduced pressure machine etc.Baking temperature is preferably 60 ℃～150 ℃.And, can also before forming photographic layer 140, on conductive base 120, form middle layer 160.At this moment, through making each the composition dissolving that contains in the middle layer 160 or being dispersed in the above-mentioned solvent, coating fluid is used in the preparation middle layer, and this coating fluid is coated on the conductive base 120, carries out drying, forms middle layer 160 thus and gets final product.The preparation method of coating fluid, coating process, drying condition etc. are identical when forming photographic layer.
(laminated electrophotographic photoreceptor)
At first, through making each the composition dissolving that contains in the charge generating layer 240 or being dispersed in the above-mentioned solvent, the preparation charge generating layer is used coating fluid.Likewise, through making each the composition dissolving that contains in the charge transport layer 220 or being dispersed in the above-mentioned solvent, the preparation charge transport layer is used coating fluid.
Then, on conductive base 120, be coated with above-mentioned each coating fluid successively and carry out drying, form charge generating layer 240 and charge transport layer 220 thus.
To the coating of each coating fluid and dry not restriction especially of order.It is identical when in addition, the preparation method of coating fluid, coating process, drying condition etc. are with formation single-layer type photographic layer.
Further, with mono-layer electronic photographic photoreceptor 100 likewise, before forming charge generating layer 240 and charge transport layer 220, can also on conductive base 120, form middle layer 160.
[image processing system]
Fig. 3 is the synoptic diagram of an example of expression image processing system of the present invention.Image processing system 10 has Electrophtography photosensor 11 and charged elements 12, exposing unit 13, developer roll 14, transfer roll 15, the cleaning unit 16 around this Electrophtography photosensor 11 that is made up of mono-layer electronic photographic photoreceptor 100 or laminated electrophotographic photoreceptor 200.
Exposing unit 13 is for forming the unit of electrostatic latent image through being made public in the surface of Electrophtography photosensor 11.Developer roll 14 is for to use toner with the roller of latent electrostatic image developing as toner image.
Usually, the electric lights etc. of removing that the surface electric charge of removing Electrophtography photosensor is set remove electric unit more in the image processing system.
But,, be difficult for accumulating the electric charge that produces through exposure in photographic layer inside because image processing system of the present invention possesses Electrophtography photosensor of the present invention.Therefore, even do not remove electricity, Electrophtography photosensor in next one circulation when charged, little as the exposure portion of exposed areas with surface electrical potential difference as the non-exposure portion in unexposed zone.Therefore, need not to be provided with and remove electric unit, can cut down preparation cost.
More than in the image processing system of explanation,, can obtain high quality images owing to use the Electrophtography photosensor of the present invention of the excellent ISO of electrical characteristics.In addition, even Electrophtography photosensor of the present invention also can be kept electrical characteristics under hot and humid environment, therefore obtain high quality images.
As this image processing system, can enumerate duplicating machine, facsimile recorder, laser beam printer etc.
[synthesizing of cavity conveying agent]
< synthesizing of compound (1-2) >
Operation (a):
In the 200mL flask, add compound (31-1) 16.1g (0.1mol) and triethyl phosphite (32) 24.9g (0.15mol), stirred 8 hours in the time of 180 ℃ of following heating.After being cooled to room temperature, excessive triethyl phosphite (32) is removed in decompression distillation, obtains white liquid compound (33-1) 22.3g.
Operation (b):
At first, adding is had N, the 500mL flask of dinethylformamide 100ml and compound (33-1) 22.3g when carrying out ice bath, drips NaOMe28%MeOH solution 16.4g (0.085mol) under argon atmospher, and 0 ℃ was stirred 1 hour down.After the stirring, in reactant liquor, drip DMF (dimethyl formamide) the solution 50ml of compound (34-1) 10.3g, stirred 12 hours under the room temperature.Reactant liquor is injected among the water 200ml, after extracted in toluene, with deionized water wash 3 times.Behind the anhydrous sodium sulfate drying organic layer, distillation removes and desolvates.Make its crystallization with toluene, methyl alcohol, obtain compound (35-1) 9.8g of faint yellow crystallization thus.
Operation (c):
In the there-necked flask of 300mL, add compound (35-1) 9.8g (0.034mol), (2-xenyl) dicyclohexylphosphontetrafluoroborate 0.098g (0.28mol), three (dibenzalacetones), two palladiums (0) 0.128g (0.14mol), sodium tert-butoxide 6.34g (0.066mol) and as the P-nethoxyaniline 4.2g (0.034mol) of compound (36-1); After distilling; Add o-xylene 200mL; Carry out argon replaces, stirred 5 hours in the time of 120 ℃ of following heating.After being cooled to room temperature, reactant liquor (organic layer) with ion-exchange water washing 3 times, is added anhydrous sodium sulfate and atlapulgite in organic layer, carry out drying and adsorption treatment thus.Then, after filtering, decompression distillation removes removal xylene, and (the expansion solvent: purifying chloroform/hexane) obtains compound (37-1) 10.2g of orange solids shape to residue thus with column chromatography.
Operation (d):
To adding compound (37-1) 10.2g (0.027mol), compound (38-1) 5.9g (0.03mol), p-toluenesulfonic acid 0.015g and toluene 100mL with in the 300mL flask of Dean-Stark separation vessel, 130 ℃ were stirred 3 hours down.After being cooled to room temperature, reactant liquor (organic layer) is injected in the ion exchange water, be dissolved in the solid of separating out in the chloroform after, with ion-exchange water washing 3 times, in chloroformic solution, add anhydrous sodium sulfate and atlapulgite, carry out drying and adsorption treatment thus.Then, after filtering, toluene is removed in decompression distillation, and (launch solvent: toluene/hexane) purifying obtains compound (1-2) 10.5g of orange solids shape to residue thus with column chromatography.
< synthesizing of compound (1-1) >
In operation (c), use para-totuidine 3.6g (0.034mol) to substitute the P-nethoxyaniline compound as compound (36-1), likewise synthetic with compound (1-2) in addition, obtain compound (1-1) thus.
< synthesizing of compound (1-3) >
In operation (c), use 4-methoxyl-2-aminotoluene 4.7g (0.034mol) to substitute the P-nethoxyaniline compound as compound (36-1), likewise synthetic with compound (1-2) in addition, obtain compound (1-3) thus.
< synthesizing of compound (1-4) >
In operation (b), use compound (34-2) 12.4g to come alternative compounds (34-1), likewise synthetic with compound (1-2) in addition, obtain compound (1-4) thus.
< synthesizing of compound (1-5) >
In operation (c), use aniline 3.2g (0.034mol) to substitute the P-nethoxyaniline compound as compound (36-1), likewise synthetic with compound (1-4) in addition, obtain compound (1-5) thus.
< synthesizing of compound (1-6) >
In operation (c), use 4-methoxyl-2-aminotoluene 4.7g (0.034mol) to substitute the P-nethoxyaniline compound as compound (36-1), likewise synthetic with compound (1-4) in addition, obtain compound (1-6) thus.
[synthesizing of charge generating (titanyl phthalocyanine)]
(pigmentation pre-treatment)
In the flask that argon replaces is crossed, add phthalonitrile 22g, four titanium butoxide 25g, urea 2.28g and quinoline 300g, be warming up to 150 ℃ in the time of stirring.Then, be warming up to when the steam that produces from reaction system is removed in distillation outside system 215 ℃ make its reaction after, when keeping this temperature, further stir and made its reaction in 2 hours.Reaction begins to cool down after finishing, and takes out reaction mixture in the moment that is cooled to 150 ℃ from flask, filters through glass filter, obtains solid.The solid that obtains is used N successively, and after dinethylformamide and the methanol wash, vacuum drying obtains hepatic solid 24g thus.
The hepatic solid 10g that obtains is joined N, among the dinethylformamide 100mL, be heated to 130 ℃ in the time of stirring, 130 ℃ of following stir process 2 hours.Then, after stopping heating through moment of 2 hours, being cooled to 23 ± 1 ℃, stop to stir, under this state, leave standstill liquid and carried out stabilization processes in 12 hours.Then, the supernatant after the stabilization is filtered through glass filter, the solid that obtains with methanol wash after, carry out vacuum drying, obtain the coarse crystallization 9.83g of titanyl phthalocyanine compound thus.
(pigmentation processing)
The coarse crystallization 5g of the titanyl phthalocyanine compound that obtains joined make its dissolving among the concentrated sulphuric acid 100mL.
Then, be added to this drips of solution in the water under ice-cooled after, at room temperature stirred 15 minutes, and then near 23 ± 1 ℃, left standstill 30 minutes, make its recrystallization, thus separation of supernatant.Then, filter above-mentioned supernatant with glass filter and obtain solid, this solid that obtains is washed after cleansing solution is neutrality, do not carry out drying, under having the state of water, be distributed among the chlorobenzene 200mL, be heated to 50 ℃, stirred 10 hours down at 50 ℃.Then, obtain solid, this solid that obtains 50 ℃ of following vacuum drying 5 hours, is obtained crystallization (blue powder) 4.1g of titanyl phthalocyanine (11-2) thus through the glass filter filtering supernatant.
To the titanyl phthalocyanine (11-2) that obtains, after just synthesizing and 1, dipping carried out CuK α characteristic X ray diffracting spectrum respectively and measures and differential scanning calorimetric analysis after 7 days in 3-dioxolanes or the tetrahydrofuran.Its results verification in CuK α characteristic X ray diffracting spectrum is measured, does not all produce the peak Bragg angle 2 θ ± 0.2 °=7.4 ° and 26.2 °.In addition, in differential scanning calorimetric analysis, when being warming up to 400 ℃, near the peak produce along with the gasification of planar water 90 ℃, all under 296 ℃, observe a peak.
[test 1: laminated electrophotographic photoreceptor]
< embodiment 1 >
(manufacturing of laminated electrophotographic photoreceptor)
The formation in middle layer:
Use ball mill to make titanium dioxide (after with aluminium oxide and silicon dioxide the SMT-02 (the number average primary particle size is 10nm) of TAYCA corporate system being carried out surface treatment; The titanium dioxide that carries out wet type to carry out surface treatment with the hydrogenated methyl polysiloxane when disperseing and obtain) 280 mass parts, copolyamide resin (DAICEL DEGUSSA corporate system " ダ イ ア ミ De X4685 ") 100 mass parts are dispersed in ethanol 1000 mass parts and butanols 200 mass parts, mix 5 hours.Then, filter, prepare the middle layer thus and use coating fluid with the filtrator of 5 μ m.
Under the state that an end of the aluminum drum type matrix that makes diameter 30mm as conductive base, total length 238.5mm makes progress; Begin to make this drum type matrix be immersed in the middle layer from the other end, thus the middle layer is applied on the conductive base with coating fluid with the coating fluid with the speed of 5mm/ second.Then, under 130 ℃, 30 minutes condition, heat-treat, form the middle layer of thickness 1.5 μ m thus.
The formation of charge generating layer:
After making previous synthetic titanyl phthalocyanine (11-2) 100 mass parts, disperse through ball mill as polyvinyl butyral resin (electrochemical industry society system, " デ Application カ Block チ ラ one Le 6000C ") 100 mass parts of binding resin, as propylene glycol monomethyl ether 4000 mass parts of dispersion medium and tetrahydrofuran 4000 mass parts as charge generating; Mixed 2 hours, and prepared charge generating layer thus and use coating fluid.
After the charge generating layer that obtains filtered with the filtrator of 3 μ m with coating fluid, be coated on dip coating on the middle layer of above-mentioned manufacturing, then 50 ℃ dry 5 minutes down, form the charge generating layer of thickness 0.3 μ m thus.
The formation of charge transport layer:
Will be with roller mill as compound (1-1) 70 mass parts of cavity conveying agent, as the viscosity average molecular weigh 50 of binding resin; 500 polycarbonate resin (13-1), 100 mass parts, mix as tetrahydrofuran 430 mass parts of solvent and toluene 430 mass parts; Make its dissolving with 24 hours, prepare charge transport layer thus and use coating fluid.
With charge generating layer with coating fluid likewise, the charge transport layer that obtains is coated on the charge generating layer with coating fluid, then 130 ℃ dry 30 minutes down, form the charge transport layer of thickness 20 μ m thus, thereby make laminated electrophotographic photoreceptor.
(estimate 1: the evaluation of light sensitivity)
Then, as follows the light sensitivity characteristic of the above-mentioned Electrophtography photosensor that obtains is estimated.That is, use drum sensitivity test machine (GENTEC corporate system) to make the electrophotographic photoreceptor belt electricity to-700V.Then, use monochromatic light (half range value 20nm, the light quantity 1.5 μ J/cms of BPF. through irradiation from the wavelength 780nm of the light taking-up of halide lamp
2), make Electrophtography photosensor exposure [irradiation time: 0.08 second (80ms)].Then, measure and to begin surface potential (rest potential) through the moment of 0.33 second (330ms) from exposure, with it as light sensitivity.The result is as shown in table 1.
< embodiment 2～9, comparative example 1～3 >
As shown in table 1, agent prepares charge transport layer and uses coating fluid as cavity conveying to use compound (1-2)～(1-9) alternative compounds (1-1) respectively, likewise makes laminated electrophotographic photoreceptor with embodiment 1 in addition, and estimates.The result is as shown in table 1.
In comparative example 1～comparative example 3, use following compound (1-7)～(1-9) as the cavity conveying agent.
[table 1]
Can be known that by table 1 laminated electrophotographic photoreceptor that obtains in the laminated electrophotographic photoreceptor that obtains among embodiment 1～embodiment 6 and the comparative example 1～comparative example 3 is compared, light sensitivity is good, and electrical characteristics are excellent.The laminated electrophotographic photoreceptor that obtains in comparative example 1～comparative example 3 is compared with embodiment 1～embodiment 6, and light sensitivity is poor.
< test 2: mono-layer electronic photographic photoreceptor >
< embodiment 7 >
(manufacturing of mono-layer electronic photographic photoreceptor)
The formation in middle layer:
The aluminum drum type matrix that uses diameter 30mm, total length 247.5mm likewise carries out with embodiment 1 as conductive base in addition, on conductive base, forms the middle layer of thickness 1.5 μ m.
The formation of photographic layer:
Will be as x type metal-free phthalocyanine (11-1) 3 mass parts of charge generating, as compound (1-1) 50 mass parts of cavity conveying agent, as compound (12-1) 40 mass parts of electron transporting agent, as meta-terphenyl 3 mass parts of the biphenyl derivatives of adjuvant, as the viscosity average molecular weigh 30 of binding resin; 500 polycarbonate resin (12-1), 100 mass parts and be contained in the ultrasonic dispersing machine as tetrahydrofuran 600 mass parts of solvent after; Mix making its dissolving in 10 minutes, prepare photographic layer thus and use coating fluid.
Then, the photographic layer that obtains formed be coated on the middle layer with dip coating with coating fluid, 130 ℃ of following heated-air dryings are 40 minutes afterwards, form the photographic layer of thickness 25 μ m thus.Thereby, make mono-layer electronic photographic photoreceptor.
(estimate 4: the evaluation of light sensitivity)
Then, as follows the light sensitivity characteristic of the above-mentioned Electrophtography photosensor that obtains is estimated.That is, use drum sensitivity test machine (GENTEC corporate system) to make the electrophotographic photoreceptor belt electricity, likewise estimate with embodiment 1 in addition to 700V.The result is as shown in table 1.
< embodiment 8～12, comparative example 4～6 >
As shown in table 2, agent prepares charge transport layer and uses coating fluid as cavity conveying to use compound (1-2)～(1-9) alternative compounds (1-1) respectively, likewise makes mono-layer electronic photographic photoreceptor with embodiment 7 in addition, and estimates.The result is as shown in table 2.
[table 2]
Can be known that by table 2 mono-layer electronic photographic photoreceptor that obtains in the mono-layer electronic photographic photoreceptor that obtains among embodiment 7～embodiment 12 and the comparative example 4～comparative example 6 is compared, light sensitivity is good, and electrical characteristics are excellent.The mono-layer electronic photographic photoreceptor that obtains in comparative example 4～comparative example 6 is compared with embodiment 7～embodiment 12, and light sensitivity is poor.
Claims (7)
1. an Electrophtography photosensor has conductive base and is formed on the photographic layer on the said conductive base, and this photographic layer contains charge generating, contains the charge transport agent and the binding resin of cavity conveying agent, it is characterized in that,
Said cavity conveying agent contain formula (1a) or (1b) shown in enamine compound,
In the formula (1a), Ra
1For having or not having the aryl of substituent carbon number 6～30, Ra
2～Ra
6Respectively identical or different, for the alkyl of hydrogen atom, carbon number 1～12 or have or do not have the aryl of substituent carbon number 6～30, said Ra
1～Ra
6In substituting group be the alkyl of carbon number 1～12 or the alkoxy of carbon number 1～12, m, n, the o of expression substituting group repeat number is 1～4 integer,
In the formula (1b), Rb
1For having or not having the aryl of substituent carbon number 6～30, Rb
2～Rb
6Respectively identical or different, for the alkyl of hydrogen atom, carbon number 1～12 or have or do not have the aryl of substituent carbon number 6～30, said Rb
1～Rb
6In substituting group be the alkyl of carbon number 1～12 or the alkoxy of carbon number 1～12, p, q, the r of expression substituting group repeat number is 1～4 integer.
2. Electrophtography photosensor according to claim 1 is characterized in that, said general formula (1a) and (1b) in Ra
1, Rb
1For having the aryl of substituent carbon number 6～30, Ra
2, Ra
3, Rb
2, Rb
3Be the aryl of carbon number 6～30, Ra
5, Ra
6, Rb
5, Rb
6Be hydrogen atom.
3. Electrophtography photosensor according to claim 1 and 2 is characterized in that, said photographic layer is at the single layer structure that contains said charge generating, said charge transport agent and said binding resin with one deck.
4. Electrophtography photosensor according to claim 3 is characterized in that, with respect to said binding resin 100 mass parts, the content of said cavity conveying agent is 20～500 mass parts.
5. Electrophtography photosensor according to claim 1 and 2; It is characterized in that; Said photographic layer is a laminar structure, has: contain the charge generating layer of said charge generating at least and contain the charge transport layer of said charge transport agent and said binding resin.
6. Electrophtography photosensor according to claim 5 is characterized in that, with respect to said binding resin 100 mass parts, the content of said cavity conveying agent is 10～500 mass parts.
7. an image processing system is characterized in that, possesses any described Electrophtography photosensor in the claim 1～6.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2008273414A JP5355984B2 (en) | 2008-10-23 | 2008-10-23 | Electrophotographic photoreceptor and image forming apparatus provided with the same |
| JP2008-273414 | 2008-10-23 |
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| CN101727027A CN101727027A (en) | 2010-06-09 |
| CN101727027B true CN101727027B (en) | 2012-08-08 |
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| JP2018194679A (en) * | 2017-05-17 | 2018-12-06 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photoreceptor |
| JP2019078978A (en) * | 2017-10-27 | 2019-05-23 | 京セラドキュメントソリューションズ株式会社 | Electrophotographic photoreceptor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2812618B2 (en) * | 1991-09-27 | 1998-10-22 | シャープ株式会社 | Electrophotographic photoreceptor |
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| JP3649890B2 (en) * | 1998-01-26 | 2005-05-18 | 三菱製紙株式会社 | Organic photoconductive material and electrophotographic photoreceptor using the same |
| JPH11258839A (en) * | 1998-03-12 | 1999-09-24 | Mitsubishi Paper Mills Ltd | Electrophotographic photoreceptor |
| JP2000112157A (en) * | 1998-10-07 | 2000-04-21 | Mitsubishi Paper Mills Ltd | Electrophotographic photoreceptor |
| JP4245181B2 (en) * | 2006-12-29 | 2009-03-25 | シャープ株式会社 | Electrophotographic photosensitive member and image forming apparatus |
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|---|---|---|---|---|
| JP2812618B2 (en) * | 1991-09-27 | 1998-10-22 | シャープ株式会社 | Electrophotographic photoreceptor |
Non-Patent Citations (3)
| Title |
|---|
| JP特开2005-215119A 2005.08.11 |
| JP特开2005-266759A 2005.09.29 |
| JP特许第2812618号B2 1998.08.07 |
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| JP5355984B2 (en) | 2013-11-27 |
| CN101727027A (en) | 2010-06-09 |
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